Playing It Cool (2014)

(5.862) based on 774 votes
A young man meets and instantly falls in love with an engaged woman.
Directors
Release Date
Sep 26, 2014
Runtime
01h 34m
Available in streaming on

A young man meets and instantly falls in love with an engaged woman.

Top 2 Movies similar to Playing It Cool

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Back to the Future

Eighties teenager Marty McFly is accidentally sent back in time to 1955, inadvertently disrupting his parents' first meeting and attracting his mother's romantic interest. Marty must repair the damage to history by rekindling his parents' romance and - with the help of his eccentric inventor friend Doc Brown - return to 1985.
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8.3
Back+to+the+Future
Back to the Future

1985

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Three Colors: White

Polish immigrant Karol Karol finds himself out of a marriage, a job and a country when his French wife, Dominique, divorces him after six months due to his impotence. Forced to leave France after losing the business they jointly owned, Karol enlists fellow Polish expatriate Mikołaj to smuggle him back to their homeland.
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7.5
Three+Colors%3A+White
Three Colors: White

1994

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Pretty Woman

While on a business trip in Los Angeles, Edward Lewis, a millionaire entrepreneur who makes a living buying and breaking up companies, picks up a prostitute, Vivian, while asking for directions; after, Edward hires Vivian to stay with him for the weekend to accompany him to a few social events, and the two get closer only to discover there are significant hurdles to overcome as they try to bridge the gap between their very different worlds.
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7.5
Pretty+Woman
Pretty Woman

1990

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The Big Lebowski

Jeffrey 'The Dude' Lebowski, a Los Angeles slacker who only wants to bowl and drink White Russians, is mistaken for another Jeffrey Lebowski, a wheelchair-bound millionaire, and finds himself dragged into a strange series of events involving nihilists, adult film producers, ferrets, errant toes, and large sums of money.
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7.8
The+Big+Lebowski
The Big Lebowski

1998

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Match Point

Chris, a former tennis player, looks for work as an instructor. He meets Tom Hewett, a wealthy young man whose sister Chloe falls in love with Chris. But Chris has his eye on Tom's fiancee Nola.
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7.4
Match+Point
Match Point

2005

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O Brother, Where Art Thou?

In the deep south during the 1930s, three escaped convicts search for hidden treasure while a relentless lawman pursues them.
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7.3
O+Brother%2C+Where+Art+Thou%3F
O Brother, Where Art Thou?

2000

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48 Hrs.

A hard-nosed cop reluctantly teams up with a wise-cracking criminal temporarily paroled to him, in order to track down a killer.
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6.7
48+Hrs.
Take Me to Tarzana

After learning their company has been illicitly spying, collecting and selling data on them, three millennial friends band together to fight back against a lecherous boss and the company's maniacal, Tarzan-obsessed CEO.
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7.8
Take+Me+to+Tarzana
Take Me to Tarzana

2021

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Family Squares

The Worth Family has been divided for years but when the matriarch, Grandma Mabel dies suddenly, the family has to come together. The story of Family Squares takes the Worth Family on a journey discovering that not only did Grandma Mabel keep some secrets, so did everyone else. They find their way back to each other and realize that while you can’t choose your family, you can choose to be friends with them.
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4.0
Family+Squares
Family Squares

2022

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The Front

A cashier poses as a writer for blacklisted talents to submit their work through, but the injustice around him pushes him to take a stand.
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7.0
The+Front
Footloose

When teenager Ren and his family move from big-city Chicago to a small town in the West, he's in for a real case of culture shock after discovering he's living in a place where music and dancing are illegal.
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6.7
Footloose
The Piano Teacher

Erika Kohut, a sexually repressed piano teacher living with her domineering mother, meets a young man who starts romantically pursuing her.
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7.3
The+Piano+Teacher
The Piano Teacher

2001

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Stuck on You

In Martha's Vineyard, Mass., conjoined twins Walt and Bob Tenor make the best of their handicap by being the fastest grill cooks in town. While outgoing Walt hopes to one day become a famous actor, shy Bob prefers to stay out of the spotlight. When a fading Hollywood actress, Cher, decides to get her show "Honey and the Beaze" cancelled, she hires Walt -- and his brotherly appendage -- as her costars. But their addition surprisingly achieves the opposite.
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5.3
Stuck+on+You
Stuck on You

2003

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Nowhere

In Los Angeles, a colorful assortment of bohemians try to make sense of their intersecting lives. The moody Dark Smith, his bisexual girlfriend, her lesbian lover and their shy gay friend plan on attending the wildest party of the year. But they'll only make it if they can survive the drug trips, suicides, trysts, mutilations and alien abductions that occur as one surreal day unfolds.
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6.8
Nowhere
50 First Dates

Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.
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6.9
50+First+Dates
50 First Dates

2004

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Russian Dolls

Five years after their summer together in Barcelona, Xavier, William, Wendy, Martine and Isabelle reunite.
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6.7
Russian+Dolls
Russian Dolls

2005

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The Story of Adele H.

Adèle Hugo, daughter of renowned French writer Victor Hugo, falls in love with British soldier Albert Pinson while living in exile off the coast of England. Though he spurns her affections, she follows him to Nova Scotia and takes on the alias of Adèle Lewly. Albert continues to reject her, but she remains obsessive in her quest to win him over.
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6.9
The+Story+of+Adele+H.
The Story of Adele H.

1975

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The Next Best Thing

A comedy-drama about best friends - one a straight woman, Abbie, the other a gay man, Robert - who decide to have a child together. Five years later, Abbie falls in love with a straight man and wants to move away with her and Robert's little boy Sam, and a nasty custody battle ensues.
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5.3
The+Next+Best+Thing
The Next Best Thing

2000

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Sister of the Bride

After only 6 months of dating, Stephanie and Ben get engaged and are delighted to share the news. However, they hit a road bump when Stephanie’s parents show concern that the couple has moved too fast.
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6.5
Sister+of+the+Bride
Sister of the Bride

2019

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There's Something About Mary

For Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy detective he hired to find her.
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6.6
There%27s+Something+About+Mary
There's Something About Mary

1998

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Transamerica

A transgender woman takes an unexpected journey when she learns that she had a son, now a teenage runaway hustling on the streets of New York.
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7.0
Transamerica
Transamerica

2005

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Monsters, Inc.

Lovable Sulley and his wisecracking sidekick Mike Wazowski are the top scare team at Monsters, Inc., the scream-processing factory in Monstropolis. When a little girl named Boo wanders into their world, it's the monsters who are scared silly, and it's up to Sulley and Mike to keep her out of sight and get her back home.
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7.8
Monsters%2C+Inc.
Monsters, Inc.

2001

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Titanic

101-year-old Rose DeWitt Bukater tells the story of her life aboard the Titanic, 84 years later. A young Rose boards the ship with her mother and fiancé. Meanwhile, Jack Dawson and Fabrizio De Rossi win third-class tickets aboard the ship. Rose tells the whole story from Titanic's departure through to its death—on its first and last voyage—on April 15, 1912.
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7.9
Titanic
Out of Africa

Tells the life story of Danish author Karen Blixen, who at the beginning of the 20th century moved to Africa to build a new life for herself. The film is based on her 1937 autobiographical novel.
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7.2
Out+of+Africa
Out of Africa

1985

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Ghostbusters

After losing their academic posts at a prestigious university, a team of parapsychologists goes into business as proton-pack-toting "ghostbusters" who exterminate ghouls, hobgoblins and supernatural pests of all stripes. An ad campaign pays off when a knockout cellist hires the squad to purge her swanky digs of demons that appear to be living in her refrigerator.
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7.5
Ghostbusters
Ghostbusters

1984

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Life Is Beautiful

A touching story of an Italian book seller of Jewish ancestry who lives in his own little fairy tale. His creative and happy life would come to an abrupt halt when his entire family is deported to a concentration camp during World War II. While locked up he tries to convince his son that the whole thing is just a game.
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8.4
Life+Is+Beautiful
Life Is Beautiful

1997

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The Holiday

Two women, one American and one British, swap homes at Christmastime following bad breakups. Each woman finds romance with a local man but realizes that the imminent return home may end the relationship.
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7.1
The+Holiday
The Holiday

2006

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Bring It On

The Toro cheerleading squad from Rancho Carne High School in San Diego has got spirit, spunk, sass and a killer routine that's sure to land them the national championship trophy for the sixth year in a row. But for newly-elected team captain Torrance, the Toros' road to total cheer glory takes a shady turn when she discovers that their perfectly-choreographed routines were in fact stolen.
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6.2
Bring+It+On
Bring It On

2000

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Meet the Parents

Greg Focker is ready to marry his girlfriend, Pam, but before he pops the question, he must win over her formidable father, humorless former CIA agent Jack Byrnes, at the wedding of Pam's sister. As Greg bends over backward to make a good impression, his visit to the Byrnes home turns into a hilarious series of disasters, and everything that can go wrong does, all under Jack's critical, hawklike gaze.
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6.7
Meet+the+Parents
Meet the Parents

2000

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Trading Places

A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.
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7.2
Trading+Places
Trading Places

1983

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